Anonymous interview 1


What frustrates you most about your current job?

Hmm… A gnarly “root” or source for many frustrations is that leadership at various levels is addicted to making short term money, at the expense of investments that would better position the business for longer term success.

This has led to ugly, untrustworthy looking, spammy feeling interfaces that we dare not change because they’ve been A/B tested to hell and back, always optimizing for actions that earn us more money. I chatted with someone who was recently on their way out, they described folks on another team they sometimes partnered with panicking over dips in weekend traffic.

This number obsessed culture isn’t 100% pervasive, thankfully, but it’s in the minds of enough decision makers that it trickles down into our design team in the form of frustrating requirements and goals that must be met.

Does anyone make an effort to push against that culture?

Yes! Our product designers meet twice a week for a designers-only (plus me, I’m honorary haha) critique of everyone's latest work in whatever state it’s in. We often ask each other about decisions each other is making and what’s fueling them, which often leads us to the frustrating requirements. This lets the team leverage each other's strategies and talking points so designers can return to their squads they can speak up against requirements that are nudging the experience toward “worse.” Now, whether they’re successful, that’s another thing.

I think the way our teams are structured makes this challenging. Designers feel very isolated (they rarely get to pair on a project never in a squad), like they’re going it alone, despite these design-only meetings (folks sometimes can't make it due to conflicting meetings). We’re addressing this this quarter actually.

On my side, not having a squad or product-person counterpart, I try to diligently keep a record of UX wins that get baked into our components. My thinking is I want to capture stuff that’s providing a helpful experience so if ever some number-obsessed idea arises to make a change at the component level then I have some ammo to say “no, but let’s explore different solutions.”

If you founded your own software company, how would you approach it?

Gosh, I don’t know that I ever would. It seems so fraught! I would probably take a lot of inspiration from the success of @amyhoy and @alexhillman! Their big wins seem to come from:

But to not avoid your question: I would probably partner with an engineer and it would just be me and them for as long as we could stand it. Make something small. Intentionally not scale it up to some gargantuan thing. No investors. Just find a pain, write about it, build an audience, build the thing, get customers, have fun maintaining it, do that until one or both of us is tired, maybe then sell it off to someone.

Why would you want to keep the business small?

A couple reasons I think:

I guess if I ever did do some sort of software business, I’d design it in a way that kept it feeling fun for me. That’s really important with my blog and everything design-related I dabble in outside my day job. I think I’m prone to falling for the bad kind of “hustle culture.”

You know who comes to mind thinking about this is the fella who made Stardew Valley. Dude toiled, alone, for years before a playable game was published. Now that part I don’t know if I have the constitution for haha but he loves that game! Like deep in his heart. And I think he’s brought on help, but he’s really kept the spirit alive as far as I can tell. And the money really rolled in!

But I haven’t heard anything like “yeah now he’s going to open a small studio so he can produce more and faster” you know? I don’t think I’m capturing it quite right. But it seems there’s some threshold you can cross where the tail starts wagging the dog. I think I’m mostly scared of the heartbreak that must come with a project that starts out exciting and joyful going sour and being a source of bad stress and high pressure (especially if it’s my own doing, it likely would be).

What frustrates you most about the design community, however you define it?

Mmm… lots of bad framings. The “should designers name their layers” thing always devolves into (what I find) are unhelpful, unproductive conversations. It’s not an unworthy topic, I just wish folks would not take the rage bait. I don’t engage with it online.

But in real life when I talk with designers, people are kind and there’s no character limits. That’s when I find it’s easier to turn it into a discussion about “how do you make your files navigable?” or “what do your developers care about when they’re inspecting your work?” That’s the heart of it. The “should designers name their layers” thing is about what kinds of forms of communication people find valuable in the context of their team/company.

And everyone’s gonna optimize differently. The online design community misses that discussion every single time. I suspect this problem exists with other rage bait topics too. “Should designers code” is another. “Should designers become AI prompt writing specialists” will probably be a thing soon if it’s not already. There’s tons of insightful conversations to be had! Lots to teach each other. Differences to appreciate.

But no one sets up these discussions that facilitate that. They position it as black and white, all or nothing, winners and losers. There’s even some big-name influencers who stoke the low value, ragey behavior. To paraphrase Visa, “the public do not know how to be a good public.” It’s disappointing. It all comes off as immature and also very insecure to me. Schoolyard behavior. Shallow.

Do you have a sense of how these problems impact new designers?

I don’t! I am curious though. It would be interesting to find designers who mentor newer designers to see what they’ve heard. Or just find those new designers and talk to them directly.

I believe Charli Prangley has a podcast episode where she discusses the effects that the “should designers name their layers” group-rage events have on new designers. I was unclear (or I can’t remember) if her insights are from first hand anecdotes or if she was speculating.

What frustrates you when you look for jobs as a designer?

I think my job hunt gripes aren’t all that specific to being a designer. My non-design friends share the same woes as me:

Portfolio sites and “take home design challenges” are maybe unique things to job hunting as a designer, but I wouldn’t say they frustrate me.

How do you feel about portfolios and take-home challenges?

Less opinions on portfolios, but yeah for take home challenges they should be paid if it's more than an hour's work. I was really lucky once, I got a very thoughtful take home challenge but it was entirely a thought exercise. The company used it to both explain how they serve two distinct users (there's internal users at the company but external users who are paying customers) and wanted me to think through how I would serve both in my design work. That one was great! I enjoyed it, I could "work on it" any time I was awake, didn't need to be at my laptop. I’d happily do more of those in the future.

I’ve heard too many stories of designers being taken advantage of and laboring for free on a take home challenge, only for a company to take the deliverables and ghost them for the remainder of the interview process.

I also think my beef with take home assignments where something needs to be produced is they typically (from what I've heard) feel more like an exam and school and less like a real life scenario. You can’t ask for help from your would-be colleagues. You can’t check in and get critique halfway through. You’re given a brief and expected to deliver some final result. It’s weird! That’s not how real design teams operate (or should be operating, in my opinion). This has me thinking that a more helpful exercise for EVERYONE would be to schedule a two hour jam session in Figma to cooperatively build something. See what it’s like to really work together.

Do you have any helpful cynical techniques or beliefs?

I don’t think so. I think I’m more of a frustrated optimist who expects better, than I am a cynic.

If I really dig down for something I guess there’s the “if you want good jobs you gotta network, you gotta know people on the inside if you want an advantage” which you say to folks and they get defeated because “networking” sounds like a chore. But making friends is generally pretty fun! Most people want friends. Or enjoy being friendly with people. So just call it that instead. I would not have had the successes I’ve had without my friends (in my personal and professional life). Yeah I guess they’re in my “network” but that’s not how I think of it. And maybe it’s a cope, but that also takes the guilt out of it.

Like, just this week I was able to get an interview for a job because I know someone who already works for the company and they referred me to the hiring manager. I got to bypass the stack of dozens of resumes that other applicants sent in. I have an edge, but I earned it. It’s not “unfair,” I think. I do good work, I treat my friends well, I keep good friends, and we help each other when we need help. Nothing wrong with that, as long as I am not pulling ladders up behind me.

It’s vital to give back, make friends with folks, go out of my way, help them when they need it. You can’t always be taking. Do I wish the larger systems we must endure were more equitable? Yeah! Of course! But that doesn’t mean we’re helpless within them. We can still help each other find success even when the deck is stacked against us. It’s the freakin’ hero’s journey! The power of friendship!